5396-98-5Relevant academic research and scientific papers
Diversity-Oriented Synthesis of a Library of Star-Shaped 2H-Imidazolines
Yu, Xuepu,Guttenberger, Nikolaus,Fuchs, Elisabeth,Peters, Martin,Weber, Hansj?rg,Breinbauer, Rolf
supporting information, p. 682 - 690 (2015/11/17)
A library of star-shaped 2H-imidazolines has been synthesized via Debus-Radziszewski condensation from 1,2-diketones and ketone starting materials. Selective reduction of one imine group of the 2H-imidazole intermediate with LiAlH4 or catalytic flow hydrogenation furnished 2H-imidazolines, which could be conveniently diversified by reacting the amine N with electrophiles, resulting in a set of 21 amide-, carbamate-, urea-, and allylamine-containing products. In total, five points of diversification could be used, which allow the production of a set of functionally diverse compounds. The synthesis of acylated 2H-imidazolidines resulted in intrinsically labile compounds, which spontaneously degraded to acyclic derivatives, as shown for the reaction of 2H-imidazolidine with hexylisocyanate.
A sequential one-pot approach to 1,2,4,5-tetrasubstituted-2H-imidazole synthesis from disubstituted alkynes
Boominathan, Siva Senthil Kumar,Chen, Chung-Yu,Huang, Po-Jui,Hou, Ruei-Jhih,Wang, Jeh-Jeng
, p. 6914 - 6918 (2015/09/02)
A sequential one-pot approach to the tetrasubstituted 2H-imidazole scaffolds has been developed from disubstituted alkynes and structurally diverse ketones. The reaction proceeds via a diketo intermediate generated from internal alkynes followed by the addition of ammonium acetate and a suitable ketone, affording a diverse range of 2H-imidazoles. Using air-moisture stable reaction conditions and inexpensive reagents, the transformation demonstrates a broad substrate scope and good functional group compatibility.
Assisted tandem catalytic cross metathesis-oxidation: In one flask from styrenes to 1,2-diketones and further to quinoxalines
Schmidt, Bernd,Krehl, Stefan,Hauke, Sylvia
, p. 5427 - 5435 (2013/07/25)
1,2-Diketones were synthesized from styrenes by combining a cross metathesis and a Ru-catalyzed alkene oxidation to an assisted tandem catalytic sequence. The synthesis relies on the use of just one metathesis precatalyst, which was in situ converted to the oxidation catalyst by addition of an alkyl hydroperoxide as a chemical trigger and oxidant. The one-flask sequence can be extended beyond 1,2-diketones to quinoxalines, by condensation of the oxidation products with ortho-phenylenediamine.
A synthesis of the pseudopterosin A-F aglycone
Cooksey, John P.,Kocienski, Philip J.,Schmidt, Arndt W.,Snaddon, Thomas N.,Kilner, Colin A.
supporting information, p. 2779 - 2785,7 (2020/07/31)
The synthesis of the pseudopterosin A-F aglycone from 3-methylcatechol features (a) the use of asymmetric Ireland-Claisen and aryl Claisen rearrangements to install three of the four stereocentres present in the molecule and (b) an A→AB→ABC annulation strategy using ring-closing metathesis and cationic cyclisation reactions as the key steps.
Comparison of Birch with electrochemical reduction of 2,3-diphenyl-1,4- diazaspiro[4.5]deca-1,3-diene
Zhou, Yan,Andreou, Anna,Biktagirov, Eldar,Eames, Jason,Wadhawan, Jay
experimental part, p. 1493 - 1497 (2011/11/29)
Reduction of 2,3-diphenyl-1,4-diazaspiro[4.5]deca-1,3-diene is investigated both voltammetrically (glassy-carbon electrode, 20 °C, non-aqueous- solvents) and using dissolving-metals (sodium, -78 °C, tetrahydrofuran (THF)/NH3(l)). Remarkably, el
Convenient Routes to Symmetrical Benzils and Chiral 1,2-Diaryl-1,2-diaminoethanes, Useful Controllers and Probes for Enantioselective Synthesis
Corey, E. J.,Lee, Duck-Hyung,Sarshar, Sepehr
, p. 3 - 6 (2007/10/02)
Pathways for the diastereoselective preparation of chiral 1,2-diaryl-1,2-diaminoethanes from ArCOOH, ArCHO or ArBr are described.
